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【结 构 式】 
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【分子编号】64586 【品名】1-nitrosoethane 【CA登记号】 |
【 分 子 式 】C2H5NO 【 分 子 量 】59.06784 【元素组成】C 40.67% H 8.53% N 23.71% O 27.09% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：Reductive amination of 6-methoxy-1-indanone (I) with piperazine (II) in the presence of titanium isopropoxide and NaBH4 furnishes the indanyl piperazine (III). Racemic amine (III) is then resolved employing (S)-10-camphorsulfonic acid to provide the (R)-enantiomer (IV). Condensation of the optically active piperazine (IV) with ethyl isocyanate then affords the target urea (1-3).
| 【1】 Mattson, R.J.; Catt, J.D.; Keavy, D.; Sloan, C.P.; Epperson, J.; Gao, Q.; Hodges, D.B.; Iben, L.; Mahle, C.D.; Ryan, E.; Yocca, F.D.; Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett 2003, 13, 6, 1199. |
| 【2】 Mattson, R.J.; Sloan, C.P.; Catt, J.D. (Bristol-Myers Squibb Co.); Novel melatonergic indanyl piperazines or homopiperazines. CA 2175395; EP 0745597 . |
| 【3】 Mattson, R.J.; Catt, J.D. (Bristol-Myers Squibb Co.); Melatonergic indanyl piperazines. US 5780470 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 64586 | 1-nitrosoethane | C2H5NO | 详情 | 详情 | ||
| (I) | 34514 | 6-methoxy-1-indanone | 13623-25-1 | C10H10O2 | 详情 | 详情 |
| (II) | 10355 | Diethylenediamine; Piperazine | 110-85-0 | C4H10N2 | 详情 | 详情 |
| (III) | 64353 | 1-(6-methoxy-2,3-dihydro-1H-inden-1-yl)piperazine; methyl 3-(1-piperazinyl)-2,3-dihydro-1H-inden-5-yl ether | C14H20N2O | 详情 | 详情 | |
| (IV) | 64354 | 1-[(1R)-6-methoxy-2,3-dihydro-1H-inden-1-yl]piperazine; methyl (3R)-3-(1-piperazinyl)-2,3-dihydro-1H-inden-5-yl ether | C14H20N2O | 详情 | 详情 |
Extended Information